
Holiday rentals with outdoor seating in Chesterton
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chesterton
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Cabin on Swede Hill
Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Blue Birdhouse - Indiana Dunes
Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

South Shore Studio Apartment {National Park}
I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

ValpoVilla: Location, location, location!
Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

Michigan City Indiana Dunes Beach National Park
Escape to our cozy home just minutes from the stunning Indiana Dunes National Park! Located in the heart of Michigan City, this charming retreat offers a relaxing getaway Enjoy a well-furnished living area, a fully equipped kitchen, and 2 comfortable bedrooms. Outdoor Bliss: Relax on the private deck or explore our beautiful garden—ideal for unwinding. Adventure Awaits: Only a short drive from the park's sandy shores, hiking trails, Lake Michigan. **CONTACT US FOR SEASONAL DISCOUNTS**

Bro’s Place 6 mile drive to Indiana Dune’s
Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

"myhathouse" detached studio downtown Chesterton
Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

New Dunes Escape
Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Visit LakeMichigan Beach-Brewery-Casino-OutletMall
Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Secluded Modern Retreat Near Beach - "Sandlot"
Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

The Lake Escape -Cozy Lakefront Cottage Valparaiso
Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.
Popular amenities for Chesterton outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Lakefront House, Pontoon, Deck, Fire Pit & More!

Couples alert! PVT beach access, hot tub, firepit!

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

-The District 5 Schoolhouse-

Casinos, Shopping, Pets, and Parking a Plenty!

Michigan City Getaway w/Games, Ping Pong, 75"TVs

Dunes Vacation Rental
Apartment rentals with outdoor seating

1Plant MOOD FREE Wi-Fi Street Parking Washer/Dryer

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Vintage Store Loft Stay on a Rescue Farm

Cute Skylar: Valparaiso University ShortTerms

Cozy Hideaway: King Bed, Fire Pit, 7 min to beach

Cozy Chalet by Lake MI&Dunes with Fire Pit

Historic Studebaker Carriage House- Lower Level

Chandelier Suite - Beaches, Dunes, Golf, Wine Tr
Condo rentals with outdoor seating

Lakeside Serenity: One-Bedroom Villa

Updated Cottage Downtown, walk to Beach

MTM Premier Properties-on acres of tranquility

Perfect Location Condo Pools Walk to all Beach 1.5

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!

Lake Condo in the heart of Downtown New Buffalo

Uptown Penthouse on Pine:By Lake
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $246 NZD | $259 NZD | $239 NZD | $235 NZD | $303 NZD | $322 NZD | $383 NZD | $339 NZD | $290 NZD | $307 NZD | $257 NZD | $263 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals with outdoor seating in Chesterton

Total holiday rentals
Explore 30 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $152 NZD per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterton rentals

4.9 Average rating
Chesterton stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Chicago Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Louisville Holiday rentals
- Detroit Holiday rentals
- Southern Indiana Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Rentals with a fire pit Chesterton
- Pet-friendly rentals Chesterton
- Cabin rentals Chesterton
- Family-friendly rentals Chesterton
- House rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
- Rentals with a patio Chesterton
- Rentals with outdoor seating Porter County
- Rentals with outdoor seating Indiana
- Rentals with outdoor seating United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Warren Dunes State Park
- The Field Museum
- Guaranteed Rate Field
- Union Park
- University of Notre Dame
- Lincoln Park Zoo
- University of Chicago
- Brookfield Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Willis Tower




